The Zebra mussel, Dreissena polymorpha, was originally native to the Caspian Sea and the Ural River in Asia. In the nineteenth century, it spread west and now occurs in most of Europe, the western portion of the Commonwealth of Independent States (formally the Soviet Union), and Turkey. Over two decades ago, the mussels, such as zebra mussel, Dreissena polymorpha and quagga mussel, Dreissena bugensis, were introduced into North America. Their wide spread through inland waters has led to the coverage of most of eastern of US [U.S. Army Engineer Waterways Experiment Station. 1995. Zebra mussels: Biology, Ecology, and Recommended Control Strategies. Technical Note. ZMR-1-01. Zebra Mussel Research Program, Vicksburg, Miss.]. Similarly, Golden Mussel, Limnoperna fortune, affected Asian and Southern American countries (Golden Mussel—Limnoperna fortune). Asian Clam Corbicula fluminea almost spread all Asian countries and US [Non-indigenous species information bulletin: Asian clam, Corbicula fluminea (Müller, 1774) (Mollusca: Corbiculidae)]. And other mussels such unionid mussels exist in US and other countries.
The ability of the mussels to quickly colonize new areas, rapidly achieve high densities and attach to any hard substratum (e.g., rocks, logs, aquatic plants, shells of native mussels, and exoskeletons of crayfish, plastic, concrete, wood, fiberglass, pipes made of iron and polyvinyl chloride and surfaces covered with conventional paints) make them to cause serious adverse consequences. These consequences include damages of water-dependent infrastructure, increased millions of dollars in the operating expense and significant damage of the ecological systems [O'Neill, C. R., Jr. 1997, Economic impact of zebra mussels-results of the 1995 national zebra mussel information clearing house study. Gt. Lakes Res. Rev. 3, 35-44; Karatayev, A. Y., L. E. Burlakova, D. K., Padilla, 1997, the effects of Dreissena polymorpha (Pallas) invasion on aquatic communalities in eastern Europe. Journal Shellfish Research, 16, 187-203; MacIsaac, H. J., 1996. Potential abiotic and biotic impacts of zebra mussels on the inland waters of North America. American Zoology, 36, 289-299; D. P. Molloy, the potential for using biological control technologies in the management of Dreissena SPP, Journal of Shellfish Research, 1998 (17) 177-183] as well as productivity reduction which costs billions of dollars in lost revenue (Connelly, N. A., C. R. O'Neill, Jr, et al. (2007), “Economic impacts of Zebra mussels on drinking water treatment and electric power generation facilities”, Environmental Management 90:10. Economic impacts of zebra mussels on drinking water treatment and electric power generation facilities. Environmental Management 40: 105-112). Additionally, rapid invasion of aquatic ecosystems by these invasive mussels has caused decline in the richness and abundance of endemic unionid mussels, an important part of biodiversity (Ricciardi, A, Neves, R. J., Rasmussen, J. B. 1998. Impending extinctions of North American freshwater mussels (Unionidae) following the zebra mussel (Dreissena polymorpha) invasion. Journal of Animal Ecology 67: 613-619).
Management of mussels is very important for protecting water-dependent infrastructure and water ecological systems. There are many ways to reduce the populations of mussels. These methods include pre-active and reactive methods. Reactive removal includes the mechanical removal, predator removal, and chemical and biochemical removal. For example, fish, birds, crayfish, crabs, leeches and mammals have shown to predate mussels. However, it is unlikely that mussel population will be controlled by natural predation, especially in man-made structures such as pipes or pumping plants.
Application of molluscicides is another effective ways to reduce the mussel population. For example, sodium hypochlorite is a commonly used control agent in Europe, US, and Canada. However, mussels can withstand this treatment for several days by closing their shells and chlorine can be only used in pipes or ducts that contain pressure sensing or other equipment due to environmental toxicity of chlorine [U.S. Army Engineer Waterways Experiment Station. 1995. Zebra mussels: Biology, Ecology, and Recommended Control Strategies. Technical Note. ZMR-1-01. Zebra Mussel Research Program, Vicksburg, Miss.]. In addition, there are many other commercialized molluscicides such as surfactant ammonium salts, Butylated hydroxytoluene (BHT) in paints, N-triphenylmethyl-morpholine and so on. These chemicals either low selectivity or affect the water ecosystems. For example, a 4-trifluoroethyl-4-nitrophenol marketed as Bayluscide® (Bayer) is a possible candidate for control such invasive exotic species. However, the toxic mechanism of such a chemical is to affect mussel cellular respiration, which in nature will limit its selectivity between mussel and other aquatic species such as fish [Karen Perry A E John Lynn, Detecting physiological and pesticide-induced apoptosis in early developmental stages of invasive bivalves, Hydrobiologia (2009) 628:153-164; I Takougang, J Meli, F Angwafo, Field trials of low dose Bayluscide on snail hosts of schistosome and selected non-target organisms in sahelian Cameroon, Mem Inst Oswaldo Cruz, Rio de Janeiro, 2006, 101(4): 355-358].
It is crucial to manage the invasive mussels in a safe, environmental friendly and cheap manner. In order to find less harmful methods to control these invasive mussels, New York State Museum's (NYSM) Field Research Laboratory screened more than 700 bacterial isolates as potential biological control agents to be used against zebra and quagga mussels. As a result, they found an isolate, strain CL145A of Pseudomonas fluorescens, to be lethal to these mussels (see Molloy, D. P. U.S. Pat. No. 6,194,194, issued Feb. 27, 2001). This bacterium is worldwide in distribution and is present in all North American waterbodies. In nature it is a harmless bacterial species that is found protecting the roots of plants from rot and mildew. It is so ubiquitous that it is a common food spoilage organism in the average household refrigerator [Daniel P. Molloy and Denise A. Mayer, Overview of a Novel Green Technology: Biological Control of Zebra and Quagga Mussels with Pseudomonas fluorescens, Version 6: Updated Aug. 24, 2007].
Lactones, Lactams, Carbamate and Amides
Lactones are widely distributed in foods and beverages, and are also secondary metabolites of animals (e.g., sponges) and microorganisms (e.g., yeasts, fungi). Some lactones have a special aroma (e.g., gamma-decalactone), resulting in an increasing demand for natural products in food industry by the use of biotechnological processes for the production of these lactones [Mohamed Alchihab, Jacqueline Destain, Mario Aguedo, Lamia Majad, Hakim Ghalfi, Jean-Paul Wathelet, Philippe Thonart, Production of γ-Decalactone by a Psychrophilic and a Mesophilic Strain of the Yeast Rhodotorula aurantiaca, Appl Biochem Biotechnol (2009) 158:41-50]. Other functions of different lactones are associated with antibacterial activity [Ikuko Shimizu, Yasunori Isshiki, Harue Nomura, Keisuke Sakuda, Katsuya Sakuma, Seiichi Kondo, The Antibacterial Activity of Fragrance Ingredients against Legionella pneumophila, Biol. Pharm. Bull. 2009, 32(6) 1114-1117], hepatoprotective activity [Yumiko Itoh, Hiroshi Shimura, Mayumi Ito, Naoharu Watanabe, Michio Yamagishi, Masaharu Tamai and Kazunori Hanada, Novel hepatoprotective γ-lactone, MH-031, I. Discovery isolation, physicochemical properties and structural elucidation, The Journal of Antibiotics 1991, 832-837], anti-tuberculosis activity [Ma, G. Y. et al. anti-tuberculosis constituents from the stem bark of micromelum hirsutum, Planta Med. 2005, 71, 261-267], anti-HIV activity [zhang et al., sesquiterpenes and butenolides, natural anti-HIV constituents from Litse verticillata, Planta Med, 2005, 71, 452-457], sex pheromone [J. H. Tumlinson, Identification of the Female Japanese Beetle Sex Pheromone Inhibition of Male Response by an Enantiomer, Science, 1977, 197, 789-792], cytotoxic activity [Fan, X. N. et al. Chemical Constituents of Heteroplexis micocephala, J. Nat. Prod. 2009, 72, 1184-1190], signal molecules [M. K. Vinson, et al. Multiple N-acyl-L-homoserine lactone signal molecules regulate production of virulence determinants and secondary metabolites in Pseudomonas aeruginosa, Proc. Natl. Acad. Sci. USA, 1995, 92, 9427-9431] and insecticidal activity [John A. Findlay, et al., Insect toxins from spruce endophytes, Can. J. Chem. 2003, 81, 284-292],
Although lactams exist in some plants and marine organisms, they often are fungal metabolites. Many biological activities (e.g., cytotoxic and antitumor activity, angiogenesis inhibition, neuronal activity, anti-infectious activities) were reviewed in a recent publication [Bastien Nay, Nassima Riache and Laurent Evanno, Chemistry and biology of non-tetramic γ-hydroxy-γ-lactams and γ-alkylidene-γ-lactams from natural sources, Natural Product reports, 2009, 26, 1044-1062].
Carbamates exist in plants, microorganism and sponges, but fewer biological activities are reported for these compounds in comparison with lactones, amides because many of these compounds are not stable in aqueous solutions. There was one example of fungicidal activity of natural carbamates [Richard J. Clark, et al., Antifungal Alkyl Amino Alcohols from the Tropical Marine Sponge Haliclona n. sp., J. Nat. Prod. 2001, 64, 1568-1571].]. Amides are widely distributed in plants, microorganisms and sponges. For example, Scalusamide A from marine-derived fungus Penicillium citrinum exhibited antibacterial and antifungal activity [Masashi Tsuda, et al., Scalusamides A-C, New Pyrrolidine Alkaloids from the Marine-Derived Fungus Penicillium citrinum, J. Nat. Prod. 2005, 68, 273-276].
Another example of an amide is a plant-derived compound called sarmentine, which displayed a lot of bioactivities. As described in application Ser. No. 61/227,412, Jul. 21, 2009 sarmentine was first isolated from the fruit of Piper sarmentosum in 1987 [Likhitwitayawuid, K., Ruangrungsi, N, Lange, G. and Decicco, C., Structural Elucidation and Synthesis of New Components isolated from Piper Samentosum, Tetrahedron 1987 (43) 3689-3694] and also from Piper nigrum in 1988 [Kiuchi, F., Nakamura, N., Tsuda, Y., Kondo, K. and Yoshimura, H. Studies on Crude Drugs Effective on Visceral Larva Migrans. IV. Isolation and Identification of Larvicidal Principles in Pepper Chemical and Pharmaceutical Bulletin 1988(36):2452], and first synthesized in 1995 [Bernabeu, M., Chinchilla, R. and Najera, C., (2E,4E)-5-Tosyl-2,4-pentadienamides: New Dienic Sulfones for the Stereoselective Synthesis of (2E,4E)-Dienamides, Tetrahedron Letter, 1995 (36)3901-3904]. Sarmentine has been found to act as an in vivo skin antioxidant protecting photoaged skin [Cornacchione, S.; Sadick, N. S.; Neveu, M.; Talbourdet, S.; Lazou, K.; Viron, C.; Renimel, I.; de Quéral, D.; Kurfurst, R.; Schnebert, S.; Heusèle, C.; André, P.; Perrier E. In vivo skin antioxidant effect of a new combination based on a specific Vitis vinifera shoots extract and a biotechnological extract. J. Drugs in Dermatol. 2007, 6S, 8-13], display antiplatelet aggregation activity [Li, C. Y.; Tsai, W.; Damu, A. G.; Lee, E. J.; Wu, T. S.; Dung. N. X.; Thang, T. D.; Thanh, L. Isolation and identification of antiplatelet aggregatory principles from the leaves of Piper lolot, J. Agric. Food Chem. 2007, 55, 9436-9442], have antiplasmodial and antimycobacterial activities [Tuntiwachwuttikul, P.; Phansa, P.; Pootaeng-on, Y.; Taylor, W. C. Chemical constituents of the roots of Piper Sarmentosum, Chem. Pharm. Bull. 2006, 54, 149-151] and antituberculosis activity [Rukachaisirikul, T.; Siriwattanakit, P.; Sukcharoenphol, K.; Wongvein, C.; Ruttanaweang, P.; Wongwattanavuch, P.; Suksamrarn, A. Chemical constituents and bioactivity of Piper sarmentosum, J. Ethnopharmacol., 2004, 93, 173-176]. Sarmentine is used as a solubilizer of hydrophobic compounds in cosmetics and pharmaceuticals (Stephen, T.; Andrew, H. Compositions comprising macromolecular assembles of lipid surfactant, PCT Publication No. WO/2008/065451). Application Ser. No. 61/227,412, Jul. 21, 2009 further discloses that sarmentine and its analogs may be used to control plant pests.